Then I fell in love, got married, and had a baby on the way. Suddenly my interests were not about what they were before, but shifted almost unconsciously to “how well can I provide for my family”, some kind of deep programming that kicked in. With a different star to sail by, I started looking around for other programming jobs and realized that anywhere outside of games and education I could make 50% more salary. The proverbial “no-brainer”, that meant the difference between raising a child in a one-room apartment over a shared carport and renting a two-bedroom house with a yard. Goodbye games, hello credit-scoring software and Fair Isaac. Part of me still wanted to work for meaning so I tried hard and came up with “credit scoring software means that more small business owners can get the right loans faster.” Not even on the same planet as educating inner-city children. Ironically my wife had come out of exactly that environment (as a sixth-grade teacher in an impoverished part of San Francisco) into educational software. But with the need to support our children and create their future, our own lofty goals were out the window.Then came job after job, and raise after raise, and I’d totally lost connection with value in my work. We had a nice house in a nice town, and my family was happy, but I found myself in a world of steak dinners with customers from Wall Street firms, working at BEA Systems where we sold multi-million-dollar systems to the richest companies in the world. I was in an environment where all that mattered was “the software business model”, meaning generating 80% profit margins as a design center, and working from there. Nobody else talked about value or what they’d left behind either. It was 2004.
Then I got very lucky. I came within inches of leaving software and information technology altogether, really the only thing I was good at and had ever been paid for. I started programming when I was 9, and apart from washing dishes at the UCSD cafeteria and doing wet science in a neurobiology lab, even my high school and college summer jobs were in programming. I was ready to do anything else as long as it was meaningful. I suppose this is what Dante Alighieri meant when he wrote “I awoke in the middle of my life in a dark wood, and the true way was wholly lost.”
Then a mentor and close friend of mine called me from his new company – a $44B software company based in Redmond, Washington. He said, “I have the perfect job for you. You have to come see.” Now of all the companies that I would have thought would rekindle my love for software, I never would have thought it would be Microsoft. I regarded the company as representing most of what was wrong with the industry, and the “Microsoft model” was what had spawned so many imitators looking for that 80% margin rather than looking to create value for real human beings. “Being in the software business means having a license to print money” was a quote attributed by many in Silicon Valley to Microsoft.
As I started to take it seriously, I got a chance to look beyond the Fortune 500 infrastructure software into an incredibly broad range of technology designed to make people more productive and have more fun. No one was building as much different software across as many different areas as Microsoft. I could see the fun, and even the joy, in building experiences that crossed everything from mobile phones and devices to games, consoles, and even office productivity. My parents had started their own company and I could see how they struggled with bad technology, and I saw Microsoft as a company that had built itself on selling to millions of mom-and-pop companies rather than the usual suspects of financial services and telecommunications. And the role they offered was close to my heart: working with startup CEO and CTOs to help them build successful businesses through partnership with Microsoft. This was a very different company than the Microsoft of 1998 which had stolen the features, messaging and box design of my first startup, NetStudio, leaving us dead in the water as they bundled their clone “PhotoDraw” for free with Office Premium.
I took the plunge, joining my 9th software company, and before long got the chance to do one of the strangest jobs in the industry: educating the inventor of the software business model and the bastion of proprietary code that open source made sense, that people who used Linux were smart, rational, and ethical, and that we needed to really think hard and compete based on value. I argued that free software developers weren’t ignorant of intellectual property and startups were running on free software because they got more value out of it – and further, that the free software ecosystem was a very logical keiretsu that included commercial interests in a more efficient system of collaboration than any proprietary approaches yet seen. Microsoft needed to compete with Linux and Unix value, and attract the open source software developers to Microsoft technologies based on the power of their platforms to make development and distribution far easier than the alternatives.For me this was meaningful work – and in the geekiest sort of way. For all the slings and arrows it was satisfying and what I was doing mattered. I had failures and success, and sometimes repeat failures that turned into successes. I certainly didn’t do everything right and left many important things undone. But I never had to wonder if it was important or if I cared about it.
Having recovered this sense I think it will be hard if not impossible to lose it a second time. I certainly hope so. Right now I’m getting the chance to work with amazing people on a free service that is designed to help open up cloud computing and make it easy for any developer to build cloud applications more easily. We really care about getting the design right and truly believe that if we build something that’s valuable enough to enough people, the money will come. Yes, you need to build for a large enough market, and yes, you need to think about the business model… and yes, naïve idealists get eaten for breakfast in Silicon Valley. But most startups don’t succeed, and success solves everything, so you can’t plan for it. So how do you decide what you’re going to build? We’ve come at this from a lot of angles and we’ve found that the most powerful question that focused us on what matters is this:What is it that is so important that you’re willing to fail at it?